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Around this time of year, the Celebrate Osuna event would typically bring Rancho Santa Fe Association members together at the Osuna Ranch decked out in cowboy hats and boots for pony rides, rodeo games and a barbecue to commemorate an important piece of Rancho Santa Fe’s history.—Karen Billing, San Diego Union-Tribune, 18 May 2026 In part, this was because Riley, who is fifty-five, wore a gargantuan, lumpy tomato-red felt hat with a wide brim, like the cowboy hat worn by Quick Draw McGraw in the old Hanna-Barbera cartoons.—Emily Nussbaum, New Yorker, 17 May 2026 The reigning Entertainer of the Year delivered the boisterous country-rock number while joined onstage by a troupe of back-up dancers clad in all white outfits with matching cowboy hats.—Charisma Madarang, Rolling Stone, 17 May 2026 The country star and her beau coordinated in all-black ensembles, which included cowboy hats.—Emily Weaver, PEOPLE, 14 May 2026 See All Example Sentences for cowboy hat